organic compounds
2-Phenyl-1H-imidazole
aDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: h-khavasi@sbu.ac.ir
In the title compound, C9H8N2, a mirror plane lies perpendicular to the phenyl and imidazole rings and passes through the bridging C—C bond, so that the imidazole ring is disordered over two sites about the mirror plane with the equal site occupancy; the contains one half-molecule. In the crystal, adjacent molecules are linked via N—H⋯N hydrogen bonds.
Related literature
For structures of 2-phenyl-1H-imidazolium salts, see: Xia et al. (2009); Xia & Yao (2010).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S160053681104699X/xu5367sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104699X/xu5367Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681104699X/xu5367Isup3.cml
The title compound has been obtained during the stirring of 2-phenyl-1H-imidazole and aniline in 1:1 molar ration in methanol for synthesis of
of reagents. The suitable crystals for X-ray analysis were obtained by slow evaporation from methanol solution after one week (yield; 86.5%).All of the H atoms were positioned geometrically with C—H = 0.93 and N—H = 0.86 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N). The molecule is disordered over two sites in the
and H1B atom is in 50% occupancy. Friedel pairs were merged as no significant anomalous scatterings.2-Phenylimidazole, as an important compound with potential N donor atom that may contribute in classical hydrogen bonding in generation of supramolecular assemblies. There are some
reports that show 2-phenylimidazole can be protonated (Xia et al., 2009; Xia & Yao, 2010).The
of the title compound contains one half-molecule, a mirror plane passes through the C—C connecting two rings (Fig. 1). In this molecule the bond lengths and angles are within normal ranges. The imidazole and phenyl rings are nearly co-planar. The intermolecular N—H···N hydrogen bonds (Table 1) occurs in the (Table 1).For structures of 2-phenyl-1H-imidazolium salts, see: Xia et al. (2009); Xia & Yao (2010).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. The molecular structure with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level. | |
Fig. 2. Packing diagram. |
C9H8N2 | F(000) = 304 |
Mr = 144.17 | Dx = 1.26 Mg m−3 |
Orthorhombic, Ama2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: A 2 -2a | Cell parameters from 1776 reflections |
a = 10.0740 (15) Å | θ = 3.0–29.1° |
b = 18.151 (4) Å | µ = 0.08 mm−1 |
c = 4.1562 (10) Å | T = 298 K |
V = 760.0 (3) Å3 | Prism, colorless |
Z = 4 | 0.17 × 0.12 × 0.10 mm |
Stoe IPDS 2T diffractometer | Rint = 0.082 |
Graphite monochromator | θmax = 29.1°, θmin = 3.0° |
rotation method scans | h = −13→11 |
1776 measured reflections | k = −19→24 |
609 independent reflections | l = −5→4 |
304 reflections with I > 2σ(I) |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0288P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
609 reflections | Δρmax = 0.14 e Å−3 |
56 parameters | Δρmin = −0.09 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (3) |
C9H8N2 | V = 760.0 (3) Å3 |
Mr = 144.17 | Z = 4 |
Orthorhombic, Ama2 | Mo Kα radiation |
a = 10.0740 (15) Å | µ = 0.08 mm−1 |
b = 18.151 (4) Å | T = 298 K |
c = 4.1562 (10) Å | 0.17 × 0.12 × 0.10 mm |
Stoe IPDS 2T diffractometer | 304 reflections with I > 2σ(I) |
1776 measured reflections | Rint = 0.082 |
609 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.14 e Å−3 |
609 reflections | Δρmin = −0.09 e Å−3 |
56 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.8165 (3) | 0.57694 (18) | 0.2820 (10) | 0.0683 (10) | |
H1 | 0.8705 | 0.6129 | 0.1911 | 0.082* | |
C2 | 0.75 | 0.4784 (3) | 0.5302 (10) | 0.0489 (13) | |
C3 | 0.75 | 0.4087 (3) | 0.7033 (11) | 0.0484 (12) | |
C4 | 0.6328 (3) | 0.3743 (2) | 0.7893 (9) | 0.0650 (9) | |
H4 | 0.5523 | 0.3965 | 0.7387 | 0.078* | |
C5 | 0.6329 (4) | 0.3080 (2) | 0.9474 (10) | 0.0778 (12) | |
H5 | 0.5528 | 0.2858 | 1.0015 | 0.093* | |
C6 | 0.75 | 0.2743 (3) | 1.0264 (15) | 0.0799 (17) | |
H6 | 0.75 | 0.2292 | 1.1323 | 0.096* | |
N1 | 0.8591 (2) | 0.51510 (13) | 0.4384 (6) | 0.0592 (8) | |
H1B | 0.9402 | 0.5022 | 0.4716 | 0.071* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0563 (17) | 0.0625 (19) | 0.086 (3) | −0.0063 (15) | 0.0075 (18) | 0.007 (2) |
C2 | 0.038 (3) | 0.054 (3) | 0.055 (4) | 0 | 0 | −0.010 (3) |
C3 | 0.044 (3) | 0.047 (2) | 0.054 (3) | 0 | 0 | −0.014 (3) |
C4 | 0.0494 (18) | 0.069 (2) | 0.077 (2) | −0.0027 (18) | −0.001 (2) | 0.000 (2) |
C5 | 0.080 (2) | 0.071 (2) | 0.082 (3) | −0.018 (2) | 0.002 (2) | 0.003 (3) |
C6 | 0.111 (5) | 0.053 (3) | 0.076 (4) | 0 | 0 | 0.001 (3) |
N1 | 0.0398 (15) | 0.0607 (16) | 0.0771 (18) | −0.0022 (14) | 0.0056 (15) | −0.0011 (19) |
C1—C1i | 1.339 (6) | C4—C5 | 1.370 (5) |
C1—N1 | 1.367 (4) | C4—H4 | 0.93 |
C1—H1 | 0.93 | C5—C6 | 1.369 (4) |
C2—N1i | 1.341 (3) | C5—H5 | 0.93 |
C2—N1 | 1.341 (3) | C6—C5i | 1.369 (4) |
C2—C3 | 1.456 (6) | C6—H6 | 0.93 |
C3—C4i | 1.383 (4) | N1—H1B | 0.86 |
C3—C4 | 1.383 (4) | ||
C1i—C1—N1 | 108.34 (16) | C3—C4—H4 | 119.4 |
C1i—C1—H1 | 125.8 | C6—C5—C4 | 120.6 (4) |
N1—C1—H1 | 125.8 | C6—C5—H5 | 119.7 |
N1i—C2—N1 | 110.2 (4) | C4—C5—H5 | 119.7 |
N1i—C2—C3 | 124.9 (2) | C5—C6—C5i | 119.0 (5) |
N1—C2—C3 | 124.9 (2) | C5—C6—H6 | 120.5 |
C4i—C3—C4 | 117.3 (4) | C5i—C6—H6 | 120.5 |
C4i—C3—C2 | 121.4 (2) | C2—N1—C1 | 106.6 (3) |
C4—C3—C2 | 121.4 (2) | C2—N1—H1B | 126.7 |
C5—C4—C3 | 121.3 (4) | C1—N1—H1B | 126.7 |
C5—C4—H4 | 119.4 | ||
N1i—C2—C3—C4i | 180.0 (4) | C3—C4—C5—C6 | 0.4 (6) |
N1—C2—C3—C4i | 0.2 (6) | C4—C5—C6—C5i | 0.5 (8) |
N1i—C2—C3—C4 | −0.2 (6) | N1i—C2—N1—C1 | −0.3 (5) |
N1—C2—C3—C4 | −180.0 (4) | C3—C2—N1—C1 | 179.5 (4) |
C4i—C3—C4—C5 | −1.3 (6) | C1i—C1—N1—C2 | 0.2 (3) |
C2—C3—C4—C5 | 178.9 (4) |
Symmetry code: (i) −x+3/2, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N1ii | 0.86 | 2.05 | 2.891 (3) | 165 |
Symmetry code: (ii) −x+2, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C9H8N2 |
Mr | 144.17 |
Crystal system, space group | Orthorhombic, Ama2 |
Temperature (K) | 298 |
a, b, c (Å) | 10.0740 (15), 18.151 (4), 4.1562 (10) |
V (Å3) | 760.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.17 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Stoe IPDS 2T |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1776, 609, 304 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.685 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.095, 0.98 |
No. of reflections | 609 |
No. of parameters | 56 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.09 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N1i | 0.86 | 2.05 | 2.891 (3) | 165 |
Symmetry code: (i) −x+2, −y+1, z. |
Acknowledgements
The authors wish to acknowledge Shahid Beheshti University, G·C, for financial support.
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
Xia, D.-C., Li, W.-C. & Han, S. (2009). Acta Cryst. E65, o3283. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, D.-C. & Yao, J.-H. (2010). Acta Cryst. E66, o649. Web of Science CSD CrossRef IUCr Journals Google Scholar
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2-Phenylimidazole, as an important compound with potential N donor atom that may contribute in classical hydrogen bonding in generation of supramolecular assemblies. There are some crystal structure reports that show 2-phenylimidazole can be protonated (Xia et al., 2009; Xia & Yao, 2010).
The asymmetric unit of the title compound contains one half-molecule, a mirror plane passes through the C—C connecting two rings (Fig. 1). In this molecule the bond lengths and angles are within normal ranges. The imidazole and phenyl rings are nearly co-planar. The intermolecular N—H···N hydrogen bonds (Table 1) occurs in the crystal structure (Table 1).